Bouveault-Blanc reduction modified

Bouveault-Blanc reduction, modified 16, 89 Bouveault-Locquin synthesis, improved 16, 230 Bradsher reagent 5, 642 V. Braun reaction 17, 625 Bridges s. a. Ethenylene bridges, Ring —... 

Desulfonylation of a-sulfonylacetates. Desulfonylation of these substrates is not satisfactory by the usual methods (Zn-HOAc, Raney Ni-C,H5OH, sodium amalgam), but can be conducted in 70-75% yield with sodium-ethanol in THF (modified Bouveault-Blanc reduction). The substrates (2) are obtained by Wolff rearrangement of a-acyl-a-benzyl-sulfonyldiazomethanes (1).1... 

Alcohols from carboxylic acid esters Modified Bouveault-Blanc reduction... 

Although some cyclohexadienes are readily available, many can be obtained easily by Birch reduction, which involves reduction with solutions of alkali metals in liquid ammonia, a source of solvated electrons, in the presence of alcohol as a proton source.8-10 In previous years, the Bouveault-Blanc procedure, which uses sodium metal and alcohol in liquid ammonia, was frequently employed for direct reduction of aromatic esters however, it gave rise mainly to the corresponding substituted benzoic acid.11 Rabideau et al. reported a modified procedure 12 however, in our hands, this resulted in the reduction of the ester function to give benzoic acid. We have found that the Birch reduction of benzoic acid, followed by esterification, is an efficient procedure for the preparation of the corresponding 1,4-dihydro compound prior to the coordination of the arene to produce functionalized dimeric ruthenium-arene complexes.13... 

---